Trineopentylphosphine: A Conformationally Flexible Ligand for the Coupling of Sterically Demanding Substrates in the Buchwald-Hartwig Amination and Suzuki-Miyaura Reaction
Steven M. Raders; Jane N. Moore; Jacquelynn K. Parks; Ashley D. Miller; Thomas M. Leißing; Steven P. Kelley; Robin D. Rogers; Kevin H. Shaughnessy; Journal of Organic Chemistry 78 (2013) 4649–4664; doi:10.1021/jo400435z

data_4028230
_publ_contact_author_address
;Department of Chemistry
Box 870336
The University of Alabama
Tuscaloosa, AL 35487-0336
USA
;
_publ_contact_author_email       kshaughn@as.ua.edu
_publ_contact_author_fax         205-348-9104
_publ_contact_author_name        'Kevin H. Shaughnessy'
_publ_contact_author_phone       205-348-4435
_publ_section_title
;
 Trineopentylphosphine: A Conformationally Flexible Ligand for the
 Coupling of Sterically Demanding Substrates in the Buchwald-Hartwig
 Amination and Suzuki-Miyaura Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4649
_journal_page_last               4664
_journal_paper_doi               10.1021/jo400435z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C44 H80 Br2 P2 Pd2'
_chemical_formula_weight         1043.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.63(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.689(9)
_cell_length_b                   9.441(7)
_cell_length_c                   18.734(13)
_cell_measurement_reflns_used    4535
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.60
_cell_volume                     2420(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1361
_diffrn_reflns_av_sigmaI/netI    0.1407
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20501
_diffrn_reflns_theta_full        26.24
_diffrn_reflns_theta_max         26.24
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    2.487
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.1257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      0
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         4.321
_refine_diff_density_min         -3.277
_refine_diff_density_rms         0.396
_refine_ls_extinction_coef       0.030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.1236
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1655P)^2^+36.7308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3138
_refine_ls_wR_factor_ref         0.3379
_reflns_number_gt                3392
_reflns_number_total             4853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400435z_si_002_3.cif
_cod_data_source_block           9
_cod_database_code               4028230