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_4028228
_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            'C30 H66 P2 Pd'
_chemical_formula_weight         595.17
_space_group_IT_number           159
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_space_group_name_H-M   'P 3 1 c'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   9.7244(4)
_cell_length_b                   9.7244(4)
_cell_length_c                   20.4524(12)
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.42
_cell_volume                     1674.94(14)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32370
_diffrn_reflns_theta_full        35.24
_diffrn_reflns_theta_max         35.24
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      0
_exptl_crystal_description       Plate
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.240
_refine_diff_density_min         -1.613
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.33(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         4848
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0559P)^2^+0.7555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                4309
_reflns_number_total             4848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400435z_si_002_1.cif
_cod_data_source_block           7
_cod_database_code               4028228