Beyond FLP additions: FLP deprotonation and C-O bond cleavage of aliphatic, aryl and ester derived olefins
Goraya, Armaan; Ajithkumar, V. S.; Ruhlandt, Karin; Stephan, Douglas W.; McCahill, Jenny SJ; Bedi, Vaibhav; Chemical Communications  (2026) –; doi:10.1039/D6CC00412A

data_7135371
_publ_section_title
;
 Beyond FLP additions: FLP deprotonation and C-O bond cleavage of
 aliphatic, aryl and ester derived olefins.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5531
_journal_page_last               5535
_journal_paper_doi               10.1039/d6cc00412a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C12 H28 P, C27 H9 B F15'
_chemical_formula_sum            'C39 H37 B F15 P'
_chemical_formula_weight         832.502
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2025-09-12
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-11 deposited with the CCDC.	2026-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.935(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7197(10)
_cell_length_b                   14.6804(11)
_cell_length_c                   16.6983(12)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.846
_cell_measurement_theta_min      2.655
_cell_volume                     3832.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            72799
_diffrn_reflns_point_group_measured_fraction_full 0.9986
_diffrn_reflns_point_group_measured_fraction_max 0.9964
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.30
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.9398.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             1706.038
_refine_diff_density_max         0.4739
_refine_diff_density_min         -0.4487
_refine_diff_density_rms         0.0858
_refine_ls_d_res_high            0.7578
_refine_ls_d_res_low             15.6354
_refine_ls_goodness_of_fit_ref   1.0140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     517
_refine_ls_number_reflns         9195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0140
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+1.8897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                6290
_reflns_number_total             9195
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d6cc00412a2.cif
_cod_data_source_block           AG402ALLYLBENZENE_0m_a
_cod_depositor_comments
'Adding full bibliography for 7135371--7135375.cif.'
_cod_database_code               7135371
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All P(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00T(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00L(H00L), C00M(H00M), C00U(H00U), C00W(H00W), C00Y(H00Y),
 C013(H013)
2.c Idealised Me refined as rotating group:
 C01A(H01a,H01b,H01c), C01C(H01d,H01e,H01f), C01D(H01g,H01h,H01i), C01E(H01j,
 H01k,H01l), C01F(H01m,H01n,H01o), C01G(H01p,H01q,H01r), C01H(H01s,H01t,H01u),
 C01I(H01v,H01w,H01x), C01K(H01y,H,Ha)
;
_olex2_submission_special_instructions 'No special instructions were received'